my net worth went negative after 9/11/01... too much in casino stocks on margin... but got lucky on the turnaround there to at least pay off the crDt crDs... then net worth got close to 0 in 2009... so essentially it was 11 years of working and saving (most i ever made in a year was 120k but i got to write off cars/travel/etc)... then a couple big gains after covid
the problem is that i didn't follow what my own tax advice always was, if you're gonna make a million and lose a million, LOSE FIRST! that way the capital losses carry forward... i paid a bunch of taxes, and avoided selling penn/nflx when i should have... now i have a ton of losses that will do me no good
some of my stocks will turn around, but i will never be super aggressive again, so there's really no way to use up my losses on a bunch of my preferred and junk bond stuff that has gone or is going bankrupt
the problem is that i didn't follow what my own tax advice always was, if you're gonna make a million and lose a million, LOSE FIRST! that way the capital losses carry forward... i paid a bunch of taxes, and avoided selling penn/nflx when i should have... now i have a ton of losses that will do me no good
some of my stocks will turn around, but i will never be super aggressive again, so there's really no way to use up my losses on a bunch of my preferred and junk bond stuff that has gone or is going bankrupt